Press START to play | The Startup mental game
Creativity and Productivity between Big Tech and Little Tech, plus 5 strategies to master the mental game of a startup.
It is tough to describe to a non-founder the struggle I have gone through in the last 5 months.
After working at Amazon for around 2 years, I decided it was time to pursue something I had always dreamt of, so I resigned in February 2024. Given the sheer quantity of startup-related articles I had been devouring, I was already expecting it to be hard.
Launching a startup turned out to be at least as hard as I had expected. My reads weren’t lying: it quickly became the greatest challenge of my professional life.
But this had been accounted for, and I was not surprised. Quite the opposite, in fact. In the first months, I actually thought it was going to be fairly simple. “This is incredible.” - I used to think daily, overstimulated and high on my adrenaline, as I gazed at the product interface we (the team and I) were building.
Nevertheless, things became harder to manage as the project’s complexity grew. And in order to keep up with the pace, I came up with some rules for keeping productive and creative at the same time. Because when we are down to it, what truly matters in a startup is finding Product-Market-Fit and generating cash flow as fast as possible.
Productivity and creativity are no easy juggle. You may be tempted to support the corporate mantra: “Creative thinking should be used to enhance productivity” … yeah, no. We can do better than that.
You can be creative in addressing your lack of productivity, that’s for sure. But creative thinking and sending 100 emails a day cannot co-exist. Sometimes, productivity needs to be favored, and creativity is best used at a different time.
Creativity and the Cost of Flexibility
Creative founders see the opportunity and snatch it. This is what makes startups so exciting: startups are small enough to perform high-risk tests that larger companies would never undertake due to something I call “Cost of Flexibility”.
The Cost of Flexibility (COF) is what kills companies down the road, and is a direct result of the incentive schemes that are used to keep managers from making dangerous, risky bets.
When I was working at Amazon, if I had an idea to propose, I would usually get told that “all you need to do is gather the data, write a whitepaper (it’s called a “doc” at Amazon) and then present it to the right stakeholders (your manager)”.
Given the pressure to hit targets in a less-than-stellar year for my team, I managed to write one (only one in 2 years, Jesus Christ…) short whitepaper about an AI product designed to ease prospecting for new Amazon Sellers (my job revolved around growing the marketplace with fashion products). The product made use of an LLM and a scraper to shorten the time spent on manual prospecting. I called it Bullet Bill.
The paper was well received and I was even sent to the Netherlands in my second-to-last week of work at the company to help build something very similar to Bullet Bill. It was great. I could discuss the project with some of the most talented product architects in the world, but it was a workshop designed to compensate for the infamous Cost of Flexibility that affects all large companies.
Large companies adopt bureaucratic systems because the finance team likes predictability. The chaotic environment that is typical of startups soon leaves in favor of the rigorous rules that managers love. And this is even more pronounced in public companies, because investors demand a solid return on their investment.
Managers love rules because their job mainly consists in not being wrong. If a manager makes a few bad calls, then they are quickly regarded as a liability. This is the Cost of Flexibility: in large companies, people have an incentive to make no risky bets, thus lowering the potential for a reward, sure. But if a corporation is large enough, its sheer size will compensate for this risk-averse attitude.
Therefore, the Cost of Flexibility is far too high for managers to incur in potential errors. Their careers are at stake, after all. I don’t blame them. I would do the same if I wanted to become a successful manager.
Entrepreneurs, on the other hand, need to experiment as much as they can in order to find Product Market Fit (PMF) as fast as humanly possible. And they need to do this with limited resources, more often than not. This is where productive creativity comes into play: finding PMF is no easy feat and flexibility is paramount.
Productivity in chaotic environments
The exact opposite of what just outlined in the paragraph above can be observed in startups. Startups thrive when the chaos that surrounds them becomes the enabling factor to create better solutions, faster. Startups can only become productive by surrendering to the coercive creative process that the market operates. This is the daily reality of working in “Little Tech”, as Marc Andreessen and Ben Horowitz
like to call startups.
Long gone are the days of dreading to write a whitepaper to pass up the chain of command, although in hindsight it was not THAT bad after all. Startups are responsible for their own success: they can’t afford the luxury of blaming VCs, the market, or (even worse) users.
Nevertheless, what I personally love about this new chapter of my professional life is the ability to cut to the chase and build things that matter to customers. This is what we did with Microsh.
In february, I got started with developing the solution and the first thing we did was contact users when our MVP was ready.
The MVP was absolute dogshit. I personally hated it. The first 2 months were spent basically showing the product only to those users who exhibited even a remote possibility of becoming a real user down the road. Heck, I even refused to show it to some of my closest (and judgemental) friends.
And this was good. We used our creativity in a productive manner - which is exactly what larger companies strive to do.
But this is not enough. A startup needs a clear execution path that can be sustained over time, especially when it comes to generating new business.
Therefore, the startup mental game is all about giving direction to a company that is looking for a route to follow. It is maintaining a positive attitude in the face of adversity. It is experimenting everyday to seek the most productive manner of doing things.
In a startup, there is no productivity without creativity.
The 5 Strategies to master the mental game of a Startup
This is a no frills paragraph. If you want to master the mental game of a startup you should:
Test your assumptions by speaking to users, customers, and other industry insiders.
Always balance your creativity with being productive. You need both. One cannot compensate for the lack of the other.
Question the quality of the feedback you receive. Feedback is important but not all feedback is correct.
Be bold in your communication. What you tell the market is crucial for receiving the right feedback.
Force yourself to spend time alone or with people you do not work with. If you are always working and being productive, you cannot be as creative.
Are you interested in launching a product or a startup? Drop me an email. If there’s anything that I can do to help a fellow founder, I will. I know the feeling!